Drug info - Bromo-DragonFLY Drug Info

Discussion in 'Phenethylamines' started by HippieD9, Jan 9, 2005.

  1. HippieD9

    HippieD9 Gold Member

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    Please post info about Bromo-Dragonfly here.

    Can anyone add information about:
    • names / synonyms
    • molecule
    • dose
    • duration
    • side effects
    • have there been any reported incidents with this compound?
    • since when has this research chemical been available?
    • legal status
    • stability of the molecule / compound
    Experiences with Bromo-Dragonfly should be posted here: Bromo-DragonFLY (Br-DFLY) trip reports
    These documents about Bromo-Dragonfly are in the file archive

    [​IMG]

    NOTE: This compound has caused a number of deaths.

    Bromo-DragonFLY
    Chemical name: Bromo-benzodifuranyl-isopropylamine or (1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane
    Chemical formula: C13H12BrNO2
    Molecular mass: 294.15 g/mol
    Melting point: decomposes at 240 °C (hydrochloride)
    CAS number: 502759-67-3
    SMILES string: N[[email protected]](C)CC1=C(OC=C2)C2=C(Br)C3=C1C=CO3 (R-isomer)

    Bromo-DragonFLY is a psychedelic hallucinogenic drug of the phenethylamine family. Bromo-DragonFLY is an extremely potent hallucinogen, comparable in dosage to LSD, and it has an extremely long duration of action. Bromo-DragonFLY has a stereocenter and R-(-)-bromo-DragonFLY is the more active stereoisomer.

    Pharmacology
    The hallucinogenic effect of bromo-DragonFLY is mediated by its partial agonistic activity at the 5-HT2A serotonin receptor, but bromo-DragonFLY also has a high binding affinity for the 5-HT2B and 5-HT2C serotonin receptor.

    History
    Bromo-DragonFLY was first synthesized by Matthew A. Parker in the laboratory of David E. Nichols in 1998.

    Anyone know any more about this? Possibly aka Br-DFLY, difuranyl-DOB or DOB-FLY.
     
    Last edited by a moderator: Sep 10, 2017
  2. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    <H3>
    <CENTER><BIG>Dihydrobenzofuran analogues of hallucinogens.
    4. Mescaline derivatives</BIG>
    by
    Monte AP, Waldman SR, Marona-Lewicka D,
    Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE.
    Department of Medicinal Chemistry and Molecular Pharmacology,
    School of Pharmacy and Pharmacal Sciences,
    Purdue University, West Lafayette, Indiana 47907, USA.
    J Med Chem. 1997 Sep 12;40(19):2997-3008

    ABSTRACT</CENTER></H3>
    <BLOCKQUOTE><BIG><BIG>D</BIG></BIG>ihydrobenzofuran and tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in the prototypical hallucinogen, mescaline (1). Thus, 4-(2-aminoethyl)-6,7-dimethoxy-2,3-dihydrobenzofuran hydrochloride (8) and 1-(8-methoxy-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b']difuran-4-yl)-2- aminoethane hydrochloride (9) were prepared and evaluated along with 1 for activity in the two-lever drug discrimination (DD) paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg). Also, 1, 8, and 9 were assayed for their ability to displace [3H]ketanserin from rat cortical homogenate 5-HT2A receptors and [3H]8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, these compounds were evaluated for their ability to compete for agonist and antagonist binding to cells expressing cloned human 5-HT2A, 5-HT2B, and 5-HT2C receptors. Finally, agonist efficacy was assessed by measurement of phosphoinositide hydrolysis in NIH 3T3 cells expressing the rat 5-HT2A or 5-HT2C receptors. Although 1 fully substituted for LSD in the DD assays (ED50 = 33.5 mumol/kg), neither 8 nor 9 substituted for LSD, with just 50% of the rats administered 8 selecting the drug lever, and only 29% of the rats administered 9 selecting the drug lever. All of the test compounds had micromolar affinity for the 5-HT1A and 5-HT2A receptors in rat brain homogenate. Curiously, the rank order of affinities of the compounds at 5-HT2A sites was opposite their order of potency in the behavioral assay. An evaluation for ability to stimulate phosphoinositide turnover as a measure of functional efficacy revealed that all the compounds were of approximately equal efficacy to serotonin in 5-HT2C receptors. At 5-HT2A receptors, however, 8 and 9 were significantly less efficacious, eliciting only 61 and 45%, respectively, of the maximal response. These results are consistent with the proposed mechanism of action for phenethylamine hallucinogens, that such compounds must be full agonists at the 5-HT2A receptor subtype. In contrast to the 2,5-dimethoxy-substituted phenethylamines, where rigidification of the methoxy groups had no deleterious effect on activity, the loss of activity in the 3,4,5-trioxygenated mescaline analogues may suggest that the 3 and 5 methoxy groups must remain conformationally mobile to enable receptor activation. </BLOCKQUOTE>
     
  3. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    More info is to be found here: http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/j m9803525


    You need to purchase the document(pdf).


    Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.

    Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE.


    Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.

    The affinity of ligands for either the 5-HT(2A) or 5-HT(2C) agonist binding site was enhanced by modification of the 2,5-oxygen substituents that are found in typical hallucinogenic amphetamines such as 4b (DOB). Restriction of the conformationally flexible 2,5-dimethoxy substituents into fused dihydrofuran rings generally resulted in increased potency relative to the parent 2,5-dimethoxy compounds. The pure enantiomers of these arylalkylamines were obtained by enantiospecific synthesis that involved acylation of the heterocyclic nucleus 7 with N-trifluoroacetyl-protected D- or L-alanyl chloride, followed by ketone reduction and N-deprotection. The enantiomers demonstrated modest stereoselectivity at the two receptors. Several general trends within these classes of new compounds were observed during their pharmacological investigation. For most pairs of optical isomers tested, the R-enantiomers of the compounds containing heterocycle 7 bound with only slightly higher affinity than their S-antipodes at the 5-HT(2A) and 5-HT(2C) receptors. Likewise, functional studies indicated that the R-enantiomers generally displayed increased potency compared to the S-enantiomers. Aromatization of the dihydrofuran rings of these arylalkylamines further increased affinity and potency. Only a few compounds were full agonists with most of them possessing intrinsic activities in the range of 60-80%. These compounds with a fully aromatic linear tricyclic nucleus are some of the highest-affinity ligands for the 5-HT(2A) receptor reported to date.



    [​IMG]


    Bromo-DragonFLY IUPAC nomenclature, Chemical nameBromo-benzodifuranyl-isopropylamine or(1-(8-bromobenzo[1,2-''b'';4,5-b']difuran-4-yl)-2-aminopropane Chemical formulaC13H12BrNO2 Molecular mass294.15 g/mol Melting pointdecomposes at 240 °C (hydrochloride) CAS registry number, CAS number- Simplified molecular input line entry specification, SMILESN[[email protected]](C)CC1=C(OC=C2)C2=C(Br)C3=C1C=CO3 (''R''-isomer) Image:R-<B style="COLOR: black; : #ffff66">Bromo-DragonFLY[/B].png, chemical structure of (''R'')-<B style="COLOR: black; : #ffff66">Bromo-DragonFLY [/B]<B style="COLOR: black; : #ffff66">Bromo-DragonFLY[/B] is a psychedelic hallucinogenic drug of the phenethylamine family. <B style="COLOR: black; : #ffff66">Bromo-DragonFLY[/B] is a the most potent known hallucinogen, it is even more potent than LSD but it has an an extremely long duration of action. <B style="COLOR: black; : #ffff66">Bromo-DragonFLY[/B] has a stereocenter and ''R''-(-)-<B style="COLOR: black; : #ffff66">bromo-DragonFLY[/B] is the more active stereoisomer. Pharmacology The hallucinogenic effect of <B style="COLOR: black; : #ffff66">bromo-DragonFLY[/B] is mediated by its partial agonistic activity at the 5-HT2A 5-HT receptor, serotonin receptor, but <B style="COLOR: black; : #ffff66">bromo-DragonFLY[/B] also has a high binding affinity for the 5-HT2B and 5-HT2C serotonin Receptor (biochemistry), receptor. History <B style="COLOR: black; : #ffff66">Bromo-DragonFLY[/B] was first synthesized by Matthew A. Parker in the laboratory of David E. Nichols in 1998. See also * 2,5-dimethoxy-4-bromoamphetamine, DOB * PiHKAL External links References * 'A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor' by M. A. Parker, D. Marona-Lewicka, V. L. Lucaites, D. L. Nelson, and D. E. Nichols in ''J. Med. Chem.'' 41(26): 5148-5149 (1998) [http://dx.doi.org/10.1021/jm9803525 DOI: 10.1021/jm9803525] * 'Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT2A/2C receptor agonists' by J. J. Chambers, D. M. Kurrasch-Orbaugh, M. A. Parker, and D. E. Nichols in ''J. Med. Chem.'' 44(6): 1003-1010 (2001) [http://dx.doi.org/10.1021/jm000491y DOI: 10.1021/jm000491y] Categorization {{Hallucinogenic phenethylamines}} ...
     
  4. HippieD9

    HippieD9 Gold Member

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    So it seems to me that this stuff would blow away anything else out there, at least in terms of strength. Anyone know of any experiance reports? It seems to me that this really needs to be investigated.





    Peace,


    D.
     
  5. Labrat

    Labrat Newbie

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    I for one hopes this one never ever enters the market.Even more sofor the longer lasting trifluoromethyl analogue. They are just way too potent to be handled by idiots. Regular LSD is very benign as far as toxicity goes. The PEA's and amphetaminesare hits another level of toxicity.
     
  6. anj0vis

    anj0vis Gold Member

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    Since this is potent enough for blotters, it will surface on the
    streets pretty soon. There are more than enough of people that want to
    make big bucks and what would be better (I don't think so, but I bet
    many do) than sell sheets of "acid".



    What comes to toxicity, sure nothing has been tested, but since this
    would work in µg doses, there are very good reasons why it would have
    very low toxicity (or at least very low ld50). It would be very
    unpropable that it would act on other receptors as powerfully as in
    5ht2 (which in itself is rather safe in actions). Only real problem,
    safety-wise, as I see it is the length of the experience. It might
    caught many people by surprise negatively.
     
  7. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    From that commercial point of view you would also want satisfied customers with high return sales and low risk on bad experiences. A strong effect with long duration will likely give exactly the opposite. Duration is exactly what made mushrooms so popular and reduced the popularity of LSD.
     
  8. HippieD9

    HippieD9 Gold Member

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    Not sure about others but I consider duration a positive, longer is better. Then again I don't use these drugs like most people do. I could see a lot of people freaking out on this, I'm sure that if it appears on the streets it'll be scheduled real quick. Unfortunatly it's impossible to keep drugs in the educated Research Chemical community. [​IMG]That all being said, I can't wait to get my hands on this if it ever is available.





    Peace,


    D.
     
  9. Triple7

    Triple7 Gold Member

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    here is another fly.. which is much less potent.. i know nothing about
    chemistry.. but i am just curious why the aromatized rings that make a
    dragon makes something much more potent.



    http://www.nis.atr.jp/~ray/pubs/Tucson04/2C-B-fly.html



    anyone who can pm some 'biochem drug sites for an compleete idiot' who likes ot learn?? you guys are talking too much chinese.
     
  10. Nagognog2

    Nagognog2 Iridium Member

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    Hmmm... I smell another STP disaster on the horizon. I can just see people taking a hit of this and, expecting LSD-effects in 15 or 20 minutes, doubling and tripling the dose. Get out the margarine ambulance and the BIG bottle of valium.
     
  11. fastandbulbous

    fastandbulbous Titanium Member

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    but i am just curious why the aromatized rings that make a dragon makes something much more potent.


    ------------------------------------------------------------ -





    It's because the fully aromatic dragonfly molecules are planar, and that allows the best conformation for binding to the 5HT2a receptor. LSD has most of all four ring systems in the same plane because the aromatic pi electrons are conjugated all the way up to the carboxyl group of the amide function (keto-enol tautomerism)
     
  12. HippieD9

    HippieD9 Gold Member

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    Just found this lil tidbit, I can't wait for this book!





    From the working draft of an upcoming book by Shulgin, "Psychedelic Index", Transform Press, 2004



    <CENTER>[​IMG]</CENTER>


    Names:


    2C-B-FLY
    1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane


    Registry Numbers:


    CARN
    HCL salt 178557-21-6


    Natural sources:


    Not known in nature


    Synthesis:


    From hydroquinone (with 1-chloro-2-bromoethane) to 1,4-bis(2-chloroethoxy)benzene (with Br2) to 1,2-bis(2-chloroethoxy)-2,5-dibromobenzene (with BuLi) to 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with dichloromethyl methyl ether) to 4-formyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with CH3NO2) to 4-(2-nitro-1-ethylene)-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with LAH) to 1-(2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane (with Br2) to 2C-B-FLY (Monte, et al., 1996).


    History:


    The "FLY" name was inspired by the two dihydrofuran rings that extend oppositely from the sides of the benzene ring. When they are aromatized (furan rings) they are planar with the benzene ring and the code name is "DRAGONFLY" and they are listed as DFLY derivatives.


    Physical properties:


    C12 H14 Br N O2
    HCl salt m.p. &gt;310 (EtOH, EtOAc) (Monte, et al. 1996).


    Pharmacology:


    The five "FLY" compounds (2C-FLY, 2C-B-FLY, FLY, B-FLY and DOM-FLY) were assayed in a drug discrimination paradigm with LSD-trained rats, and in interactions with various serotonin receptors. (Monte, et al., 1996).
    2C-B-FLY is active in man at an oral dose of 10 milligrams (Shulgin, 2003a)


    Legal Status:


    2C-B-FLY is not listed in any law.
     
  13. anj0vis

    anj0vis Gold Member

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    I wonder why DOM-FLY is not called D-FLY or M-FLY, since that would be more logical (like following 2C-D nomenclature or then using the logical M for Methyl). 2C refers to phenethylamine and obviously B-FLY is the amphetamine analogue (should be DOB-FLY if written like DOM-FLY).
     
  14. fastandbulbous

    fastandbulbous Titanium Member

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    It would definitely make for some of the stranger names, if you start considering the benzodifuran derivatives of the beta-methoxy compounds from PIHKAL.


    You end up with BOB-FLY and BOD-FLY (the second one based on the DOM ring substitution pattern sounds like somthing that carries nasty diseases!)
     
  15. Nagognog2

    Nagognog2 Iridium Member

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    I assume in case of a bad trip on BOD-FLY, one would then reach for the BLACK-FLAG. And if it were to be outlawed, you could expect RAID.
     
  16. ChemicallyBound

    ChemicallyBound Gold Member

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    From hydroquinone (with 1-chloro-2-bromoethane) to 1,4-bis(2-chloroethoxy)benzene (with Br2) to 1,2-bis(2-chloroethoxy)-2,5-dibromobenzene (with BuLi) to 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with dichloromethyl methyl ether) to 4-formyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with CH3NO2) to 4-(2-nitro-1-ethylene)-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with LAH) to 1-(2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane (with Br2) to 2C-B-FLY (Monte, et al., 1996).


    _________________________________________________________


    Not an absolutely bad synth route at all!


    BUT, it is not active apparently in sub 10mg levels in humans as previously thought even though it is the most potent 5HT-2 binding affinity there is.
     
  17. fastandbulbous

    fastandbulbous Titanium Member

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    BUT, it is not active apparently in sub 10mg levels in humans as previously thought even though it is the most potent 5HT-2 binding affinity there is.


    Which, 2C-B-FLY or bromodragonfly? I ask as the bromodragonfly is active in humans at sub milligram levels (I've heard nowt about the human dose of the phenethylamine though)
     
  18. anj0vis

    anj0vis Gold Member

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    and that 2c-b-fly is the nonaromatized version, aromatized (furan rings) version is much more potent. I don't know how big difference there is, but if it is say (guessing) 5-fold, we would see activity at 2mg+, which is already quite good.
     
  19. ChemicallyBound

    ChemicallyBound Gold Member

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    Ah, the bi-furan rings are the diff. between 2c-b-fly and b-dragonfly,


    missed it at first glance. Haven't had time to look at MA Parkers route yet, I'd assume its not too different. Has this one actually been bioassayed then for definitive activity in human?
     
  20. ethacetin

    ethacetin Newbie

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    Hello, I have some questions regarding this compound.



    I read an article by David E. Nichols in which he was testing out
    conformations of the phenethylamine molecule (the article was exploring
    the possible missing link between the tryptamine and phenethylamine
    worlds) and more specifically which conformation the ethylamine chain
    preferred to be in.



    He made a series of test compounds, all resembling these DragonFLYs,
    except that he only bound the oxygen at the 5-position in a furan ring
    and left the 2-methoxy group as it was.



    I'm really sorry that i can no longer find the article, but in light of
    the trends Shulgin found in his Tweetios (2-EtO- compounds yield a
    shorter duration and a lower potency, 5-EtO- compounds have a
    relatively unchanged potency and a longer time duration, and 2,5-DiEtO-
    homologues are very weak, if active at all), i was wondering if it
    would be better to in fact leave this 2-methoxyl group alone and not
    extend it or if attaching both oxygens back to the benzene ring does in
    fact yield a more potent, longer lasting, or overall "better"
    compound.



    If anyone has any information or an opinion about this it would be greatly appreciated.



    Thanks